ethyl 4,6-dimethoxy-2,3-diphenylindol-1-ylacetate | 1100050-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 4,6-dimethoxy-2,3-diphenylindol-1-ylacetate
• 英文别名: Ethyl 2-(4,6-dimethoxy-2,3-diphenylindol-1-yl)acetate；ethyl 2-(4,6-dimethoxy-2,3-diphenylindol-1-yl)acetate
• CAS: 1100050-22-3
• 化学式: C₂₆H₂₅NO₄
• 分子量: 415.489
• InChiKey: PFDBQNCICVHIKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-dimethoxy-2,3-diphenylindol-1-ylacetate 、 N,N-二甲基甲酰胺 在 三氯氧磷 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以80%的产率得到ethyl 4,6-dimethoxy-7-formyl-2,3-diphenylindol-1-ylacetate
  参考文献：
  名称：

  Effective synthetic routes to activated pyrrolo[3,2,1-hi]indoles

  摘要：

  Pyrrolo[3,2,1-hi]indoles have been formed by the aldol cyclisation of 7-formyl-N-indolylacetates. The synthetic sequence incorporates three steps from suitably activated indoles: these are alkylation at nitrogen with a bromoacetic ester, formylation at C7 and an aldol condensation between these two substituents. Art X-ray crystal structure of pyrrolo[3,2,1-hi]indole 24 is described. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.025
• 作为产物：
  描述：

  4,6-dimethoxy-2,3-diphenyl-1H-indole 、 溴乙酸乙酯 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以86%的产率得到ethyl 4,6-dimethoxy-2,3-diphenylindol-1-ylacetate
  参考文献：
  名称：

  Effective synthetic routes to activated pyrrolo[3,2,1-hi]indoles

  摘要：

  Pyrrolo[3,2,1-hi]indoles have been formed by the aldol cyclisation of 7-formyl-N-indolylacetates. The synthetic sequence incorporates three steps from suitably activated indoles: these are alkylation at nitrogen with a bromoacetic ester, formylation at C7 and an aldol condensation between these two substituents. Art X-ray crystal structure of pyrrolo[3,2,1-hi]indole 24 is described. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.025

文献信息

• Synthetic approaches to activated pyrrolo[3,2,1-hi]indoles: synthesis of 6,8-dimethoxy pyrrolo[3,2,1-hi]indole
  作者：Jumina、Naresh Kumar、David St.C. Black

  DOI：10.1016/j.tet.2009.01.010

  日期：2009.3

  6,8-Dimethoxypyrrolo[3,2,1-hi]indole 25 has been formed by the dehydrogenation of the related tetrahydro compound 23, which in turn was formed by reduction of the related isatin 22. Approaches to achieve the cyclisation of N-hydroxyethylindoles, N-dimethylacetamidoindoles, and C7-substituted chloroacetylindoles were unsuccessful.

  通过相关四氢化合物23的脱氢反应形成了6,8-二甲氧基吡咯并[3,2,1- hi ]吲哚25，该四氢化合物23又通过相关的靛红22的还原而形成。实现N-羟乙基吲哚，N-二甲基乙酰氨基吲哚和C 7取代的氯乙酰吲哚的环化的方法是不成功的。